Реакция #73214

Уравнение реакции

3-cyclopentylidene-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

→

desired product

Выход 33.3%

3-Cyclopentylidene-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

Выход 33.3%

Растворители

DCM

TFA

Условия реакции

Обработка

1. 1
   ДругоеThe solvents were evaporated in vacuo
2. 2
   workup.ADDITIONThe reaction mixture was neutralized by dropwise addition of concentrated HCl
3. 3
   ЭкстракцияThe product was extracted with ethyl acetate
4. 4
   СушкаThe combined organic extracts were dried over sodium sulfate
5. 5
   Фильтрацияfiltered
6. 6
   Концентрированиеconcentrated in vacuo
7. 7
   ДругоеThe crude residue was purified by preparative-HPLC/MS (C18 column
8. 8
   Промывкаeluting with a gradient of ACN/H2O containing 0.15% NH4OH)

Методика

A solution of 3-cyclopentylidene-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (0.030 g, 0.069 mmol) in DCM (3 mL) and TFA (2 mL) was stirred for 1 hour. The solvents were evaporated in vacuo and the product was stirred with sodium hydroxide, 50% aqueous solution (0.75 mL) and water (0.75 mL) and THF (1.5 mL) for 2 hours. The reaction mixture was neutralized by dropwise addition of concentrated HCl. The product was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by preparative-HPLC/MS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) to afford the desired product (7 mg, 33%).

Источник